Meadowfoam sulfosuccinates

ABSTRACT

The present invention deals with the certain novel meadowfoam derived sulfosuccinates. These materials are useful as cosmetic ingredients as additives to shampoo systems where outstanding liquidity, resistance to oxidation, and minimal odor variation are required.

RELATED APPLICATIONS

This application is a continuation in part of copending application Ser.No. 692,376, filed: Jul.31, 1996 which is in turn a continuation in partof copending application Ser. No. 516,138 filed Aug. 17, 1995.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention deals with the certain novel sulfosuccinates whichare prepared by the reaction of a meadowfoam based alkanolamide, maleicanhydride and sodium sulfite. These materials are extremely mild, haveessentially no odor and therefore are useful as cosmetic ingredients.These materials have outstanding liquidity, resistance to oxidation, andminimal odor variation are required. This combination of properties makethese compounds excellent candidates as additives to personal careproducts like shampoos where they thicken formulations and stabilizefoam.

2. Description of the Art Practices

Alkanolamides perform a variety of functions including viscosityenhancement, foam stabilization, emulsification, and detergency.Chemically, alkanolamides are the reaction product of an alkanolamineand a fatty material. Fatty materials are a class of compounds whichinclude fatty carboxylic acids, fatty methyl esters and fatty glycerides(also called oils). The source of the fatty materials include coconut,peanut, soybean, and rapeseed oils, fractionated and non-fractionatedfatty methyl esters and acids of almost any carbon length.

Variation of carbon chain lengths in the fatty source has direct effectupon alkanolamide properties. While short chain fatty materials resultin compounds useful as humectants and hair anti-tangle agents, productsbased upon 8 to 10 carbon fatty acids exhibit foam stability butcontribute littie as thickeners. The medium range 12 to 14 carbon fattyacids are the best foam boosters, while also showing good viscositybuilding properties. Lauric-myristic diethanolamides are commoningredients in formulations of high foaming products such as dish washdetergent, bubble bath, and hair shampoo. They also contribute emollientand conditioning effects upon skin and hair in many formulations. Thisis why the lauric myristic alkanolamides have become the workhorse ofthe cosmetic industry.

The use of higher molecular weight unsaturated fatty alkanolamidesreduce foam and foam stabilization but give good viscosity build. Theoptimum performance in a formulation is often obtained when one employsblends of alkanolamides having differing carbon chain lengths. This canresult in the desired properties of both materials. Oleic and linoleicalkanolamides are excellent viscosity builders at low concentration inmost shampoos and are of particular interest in formulations thatcontain surfactants which are difficult to thicken. These highermolecular weight unsaturated products because of their unsaturationsuffer from oxidative instability and interfere with the fragrance ofmany products.

The recent availability of meadowfoam oil, with it's 20 to 22 carbonatoms and the specific location of it's double bonds, and it's reactionto make alkanolamides results in the preparation liquid stablealkanolamides, acceptable for use in personal care applications.

The selection of a mono-hydroxy alkanolamide as a raw material used tomake sulfosuccinates useful in hair and skin care applications. Thesulfosuccinates of the present invention have outstanding skin feel.

None of the prior sulfosuccinates possess the critical meadowfoammoiety. Molecules of the current invention have the meadowfoam alkylgroup in the alkanolamide, which is subsequentiy converted into thesulfosuccinate by the technology which will become apparent by thedisclosure of the present application.

THE INVENTION

This invention relates to a particular group of sulfosuccinates made bythe reaction of a meadowfoam oil, meadowfoam based alkanolamide. Themeadowfoam alkanolamide is the subject of the copending application fromwhich this application is a continuation in part. The terms meadowfoamoil, fatty acid or methyl ester as used herein refer to a specific alkyldistribution of the groups which is are native to a plant LimnathesAlba, commonly called meadowfoam oil. Meadowfoam oil is harvested from aplant and sold commercially by The Fanning Corporation under thetradename "Fancor Meadowfoam".

The unique structure of the oil coupled with the proper selection of thealkanolanolamide chosen to make the sulfosuccinate results in a liquidsulfosuccinate with oxidative stability and skin feel heretoforeunattainable. The fatty distribution of the oil ranges from 20 to 22carbons and has unsaturation in specific locations. The oil contains 97%by weight higher unsaturated alkyl groups. Typically, meadowfoam oilcontains 60-65% of a twenty carbon mono-carboxy acid having oneunsaturation between carbon 5 and 6. Additionally, it contains 12-20% ofa twenty two carbon mono-carboxy acid having one unsaturation betweeneither carbon 5 and 6, or carbon 13 and 14 and 15-28% of a twenty twocarbon mono-carboxy acid having one unsaturation between both carbon 5and 6, or carbon 13 and 14. The combination of the fact that there are20 to 22 carbon atoms in the group leads to lack of volatility, thepresence of unsaturation leads to liquidity and the fact that thedi-unsaturated moieties are not conjugated leads to outstandingoxidative stability.

Additional aspects of the invention is the application of thesematerials as personal care applications were the specific properties ofthe sulfosuccinate having the unique distribution of the meadowfoam onthe other result in superior liquidity, lubricity, and outstandingoxidative stability.

The compounds of the current invention are sulfosuccinates derived frommeadowfoam conforming to the following structure; ##STR1## R¹ is derivedfrom meadowfoam and specifically is 60-65% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.13--CH3

12-20% by weight a mixture of

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.15 --CH.sub.3

    and

    --(CH.sub.2).sub.11 --CH═CH--(CH.sub.2).sub.7 --CH.sub.3

and

15-28% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.6 --CH═CH--(CH.sub.2).sub.6 --CH.sub.3 ;

R² is:

    --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)O).sub.y --

x, and y are independentiy 0 or 1 with the proviso that x+ y is greaterthan 0;

M is a cation selected from K or Na.

It is also envisioned that the compounds of the present invention can beblended with other sulfosuccinates to obtain products which will haveimproved liquidity and improved viscosity build in formulations are wellas enhanced foam stabilization effects.

The invention also teaches that a sulfosuccinate can be made by thefollowing sequence of reactions: ##STR2## x, and y are independentiy 0or 1 with the proviso that x+ y is greater than 0. ##STR3##

Another aspect of the present invention is the intermediate meadowfoammaleate conforming to the following structure:

    R.sup.1 (O)C--N(H)--(R.sup.2)--C(O)--CH═CH--C(O)--OH

R¹ is derived from meadowfoam and is;

60-65% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.13--CH3

12-20% by weight a mixture of

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.15 --CH.sub.3

    and

    --(CH.sub.2).sub.11 --CH═CH--(CH.sub.2).sub.7 --CH.sub.3

and

15-28% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.6 --CH═CH--(CH.sub.2).sub.6 --CH.sub.3 ;

R² is

    --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)O).sub.y --;

x, and y are independentiy 0 or 1 with the proviso that x+ y is greaterthan 0.

In addition to being an intermediate in the preparation of thesulfosuccinates of the present invention this maleate in aqueoussolution neutralized to pH of 7 is a good anionic surfactant.

Preferred Embodiment

In a preferred embodiment M is K.

In a preferred embodiment M is Na.

In a preferred embodiment x is 1, and y is 0.

In a preferred embodiment x is 0, and y is 1.

In a preferred embodiment x is 1, and y is 1.

EXAMPLES RAW MATERIALS Meadowfoam Oil

Meadowfoam Oil can be used as a triglyceride, which is the oil asprovided, reacted with methanol in processes known to those skilled inthe art to make methyl ester, or reacted using technology known in theart to make carboxylic acids. The CAS number of meadowfoam oil is153065-40-8. The methyl ester of meadowfoam is the preferred statringmaterial.

Alkanolamines

The alkanolamides useful in the present invention have one hydroxylgroup present. They conform to the following structure: ##STR4## R² is:

    --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)O).sub.y --H

x, and y are independentiy 0 or 1 with the proviso that x+ y is greaterthan 0.

Class 1 (monoalkanolamines)

Monoalkanolamines are products of commerce and are availablecommercially from many companies like Union Carbide. R³ is H in thisclass of compounds.

    ______________________________________                                                              R.sup.2                                                 Example                     x      y                                          ______________________________________                                        1          Monoethanolamine 1      0                                          2          Monoisopropanolamine                                                                           0      1                                          3          Mixed Amine 1    1      1                                          4          Mixed Amine 2    10     10                                         ______________________________________                                    

Amide Synthesis

The amidification reaction is carried out using an excess ofalkanolamine or meadowfoam or more typically using an equivalent ofeach. The reaction can be carried out with or without catalyst.

General Procedure--Meadowfoam Methyl Ester

To the specified number of grams of alkanolamine (examples 1-6) is addedthen 354.0 grams of the meadowfoam methyl Ester. The temperature of themass is raised to 150°-200° C. The amine value drops to vanishinglysmall levels.

The products are clear liquids and are liquid to extraordinarytemperatures. They are used to make sulfosuccinates.

    ______________________________________                                                      Alkanolamine                                                    Example       Example    Grams                                                ______________________________________                                        5             1          60.0                                                 6             2          75.0                                                 7             3          118.0                                                8             4          1045.0                                               ______________________________________                                    

Maleate Synthesis

The alkanolamide examples 5, 6 and 7 are used as intermediates in thesynthesis of maleate ester which is in turn sulfonated in a latter step.The reaction sequence is as follows:

The Amide from part 1 is added to a suitable vessel. It is heated to 60°C. or until molten. Next the maleic anhydride is added slowly, keepingthe temperature between 60° and 80° C. The temperature is held for 2-3hours. The acid value is checked and when 97% of the reaction hasoccurred, the material is cooled. The material is ready for use withoutfurther processing.

    ______________________________________                                        Example        Amide Derivative                                                                            Maleic Anhydride                                 Number   Example     Grams   Grams                                            ______________________________________                                         9       5           386.0   98.0                                             10       6           401.0   98.0                                             11       7           444.0   98.0                                             12       8           1371.0  98.0                                             ______________________________________                                    

Sulfonation of the Maleate

The maleate is sulfonated in aqueous solution as follows:

To the specified amount of water is added the sulfite. Most commonlysodium sulfite is used, but potassium sulfite may also be used. Thereaction is stirred until a clear solution is obtained. The solution isheated to 80° C. and the molten maleic derivative is added. The pH iskept between 6-8 during the reaction. The reaction is held at between70° and 80° C. During that time the product becomes clear. The residualsulfite is checked by titration with iodine and becomes vanishinglysmall. The product is ready to use as prepared and may range in solidsfrom 20% to 60% with 30-40% being the preferred concentration.

    ______________________________________                                        Example Maleate Derivative                                                                           Sulfite      Water                                     Number  Example   Grams    Type   Grams Grams                                 ______________________________________                                        13       9        486.0    Na.sub.2 SO.sub.3                                                                    126.0 1530.0                                14      10        501.0    Na.sub.2 SO.sub.3                                                                    126.0 1570.0                                15      11        544.0    Na.sub.2 SO.sub.3                                                                    126.0 1675.0                                16      12        1471.0   Na.sub.2 SO.sub.3                                                                    126.0 4000.0                                17       9        486.0    K.sub.2 SO.sub.3                                                                     158.0 1610.0                                18      10        501.0    K.sub.2 SO.sub.3                                                                     158.0 1650.0                                19      11        544.0    K.sub.2 SO.sub.3                                                                     158.0 1755.0                                20      12        1471.0   K.sub.2 SO.sub.3                                                                     158.0 4075.0                                ______________________________________                                    

The products as prepared above are yellow liquids. They have very littieodor and a silky feel on the skin. In addition they are non-irritatingto the eye and skin and non-comedogenic.

I claim:
 1. A meadowfoam sulfosuccinate conforming to the followingstructure; ##STR5## R¹ is derived from meadowfoam and is 6- 65% byweight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.13--CH3

12-20% by weight a mixture of

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.15 --CH.sub.3

    and

    --(CH.sub.2).sub.11 --CH═CH--(CH.sub.2).sub.7 --CH.sub.3

and 15-28% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.6 --CH═CH--(CH.sub.2).sub.6 --CH.sub.3 ;

R² is:

    --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)O).sub.y --

x, and y are independentiy 0 or 1 with the proviso that x+ y is greaterthan 0; M is a cation selected from K or Na.
 2. A meadowfoamsulfosuccinate of claim 1 wherein M is K.
 3. A meadowfoam sulfosuccinateof claim 1 wherein M is Na.
 4. A meadowfoam sulfosuccinate of claim 1wherein x is 1, y is
 0. 5. A meadowfoam sulfosuccinate of claim 1wherein x is 0, y is
 1. 6. A meadowfoam sulfosuccinate of claim 1wherein x is 1, y is
 1. 7. A meadowfoam maleate conforming to thefollowing structure:

    R.sup.1 (O)C--N(H)--(R.sup.2)--C(O)--CH═CH--C(O)--OH

R¹ is derived from meadowfoam and is 60-65% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.13 --CH.sub.3

12-20% by weight a mixture of

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.15 --CH.sub.3

    and

    --(CH.sub.2).sub.11 --CH═CH--(CH.sub.2).sub.7 --CH.sub.3

and 15-28% by weight

    --(CH.sub.2).sub.3 --CH═CH--(CH.sub.2).sub.6 --CH═CH--(CH.sub.2).sub.6 --CH.sub.3 ;

R² is

    --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)O).sub.y --;

x, and y are independentiy 0 or 1 with the proviso that x+ y is greaterthan
 0. 8. A meadowfoam maleate of claim 7 wherein x is 1, and y is 0.9. A meadowfoam maleate of claim 7 wherein x is 0, and y is
 1. 10. Ameadowfoam maleate of claim 7 wherein x is 1, and y is 1.